Matchmaker in Heaven
by xox serendipity
Summary: Gabriella is the school's matchmaker but she's soon retiring for her Junior year. But what happens when her best friends has her eyes out for Troy Bolton? Gabriella can't help but set them up, but when feelings start to linger, what will happen? future M.
1. First Day

**AN: Hey everyone! This is my first Fanfic and it is a Troyella tale. Hopefully you like and I will keep on M for future purposes. Hope you enjoy!**

**Summary: Gabriella is a matchmaker at East High. If you have troubles finding your one true love, she's the girl to go to. So what happens when her best friend has started taking a liking to golden boy Troy Bolton? Being a good friend, Gabriella is entitled to set them together, her reputation and friendship on the line. Will this couple end in a matchmake in heaven?**

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><p>Gabriella took one last check of herself in the mirror. Turning her head to check her hair, she nodded her head and threw her jacket over her shoulder.<p>

"Gabriella, hurry up! First day back to school and you're going to be late!" her mother called up the stairs.

"Coming!" she replied, glancing at her room with a smile before closing the door behind her.

Gabriella quickly walked down the stairs, finding her mother and little sister at the kitchen table. Picking up an apple from the island, she popped it into her mouth as she put her jacket on. Taking a bite out of it, she slung her backpack strap onto her shoulder, heading out of the kitchen.

"Hold it!" Well, she was.

Her mother got up from her seat, walking towards her daughter. Gabriella turned her around so that she was facing her. Her mother was still a few inches taller than her, probably because she was wearing heels. Their deep brown hair were identical in shades and their eyes were the same chocolate brown.

"Mom, I'm going to be late! Sharpay's going to pick me up and-"

"I know, I know," her mother interrupted. "Are you going to be alright? I mean, I'm not going to be there to watch out for you since I've transferred to a new school."

Gabriella sighed and rolled her eyes, slouching her shoulders. "Mom, I've got it. I'm a big girl now, remember?"

Her mother chuckled. She kissed Gabriella on her forehead and turned around to go sit with her little sister, Maria.

"Oh, and I want you to stop with all this matchmaking business, alright? You have one year left to get into a good college so grades first and romance later," her mother called behind her.

"Yeah, right, Mom. Gabbie can't even get a boyfriend, she can only get one for other people," Maria mocked, sticking her tongue out at Gabriella.

Gabriella scoffed and rolled her eyes again. "Eat your cereal."

Maria hmph'ed and put a spoonful of Lucky Charms into her mouth.

Gabriella walked out of the kitchen and picked up her keys before slipping her shoes on and walking out the front door. Sharpay and Taylor were already parked outside and Sharpay was furiously honking her horn.

"GABRIELLA! HURRY UP!" Sharpay called.

"CALM DOWN, BLONDIE!" she screamed back, opening the door to the passenger seat and getting in.

Sharpay quickly pulled out and started driving, shocking Gabriella a bit but managed to fasten her seat belt. Taylor was sitting behind them but leaned forward so her head was in the little space between front seats.

"So, junior year. Goals?" Taylor asked the two girls.

Sharpay scoffed. "Of course I'm going to be in the winter, fall, AND spring musical. Ugh, but my brother's probably gonna be my romance interest."

Taylor and Gabriella giggled. "I'm going to focus on my grades so that means no more matchmaking anymore," Gabriella told the girls.

"WHAT? Why! You're like, amazing, no doubt. You can make anyone fall in love and I mean ANYONE," Taylor replied.

Gabriella sighed and shrugged her shoulders. "I don't know. I mean I'll give advice and stuff but I won't go full out like I used to anymore, alright?"

Taylor sighed. "Fine, but as long as we win the decathlon, then I'm perfectly okay with whatever you do."

Gabriella chuckled. "You're still going to join musicals though, right Gabriella? Because you know, every great production needs supporting characters to make the leads shine" Sharpay asked, not taking her eyes off the road but smiled widely at herself.

Gabriella smiled and rolled her eyes. Before she knew it, they were already at the school, parked in Sharpay's own parking spot. As they got out and walked towards the entrance, Gabriella took in her surroundings. Students laughing and talking, guys fooling around, and girls catching up. It was surely a high school scenario.

As the trio walked inside the school, they migrated towards their lockers that were conveniently placed next to each other's. Of course, Sharpay's had been pre-decorated which meant, rhinestones, feathers, and of course lots and lots of pink.

"So looks like we have Ms. Darbus for homeroom again," Taylor stated as all three punched in their locker combinations and emptied their backpacks inside of them.

"Joy," Gabriella said sarcastically. "Is it just me or does it feel like she's going to torture us 10 times more than in sophomore year?"

"It's just you," Sharpay said, primming and primping her hair and make-up in her locker mirror.

Taylor scoffed and rolled her eyes. "Puh-lease. The only reason you like her is because you're her absolute favorite student."

Gabriella laughed. She was putting magnets and pictures inside her locker. She heard Sharpay gasped loudly beside her and startled, widening her eyes at her.

Sharpay held onto Gabriella's arm, squeezing it tightly. "Oh my god, PINCH ME! It's Troy Bolton!" she screamed.

"Wait, what?" Gabriella mumbled to herself, holding onto her locker door as she turned her head to where Sharpay was staring at, Taylor doing the same.

There he was, the Troy Bolton: basketball star and East High's own heartthrob. His glistening brown hair fell perfectly on his head, the way his eyes peeked out from behind his bangs was adorable. His aqua orbs would enter your body and make your whole body feel like a hot mess. His smile, oh _his smile: _it was gorgeous. His teeth were pearly white and perfectly aligned. The way his lips curled and the small laugh he did beforehand would send you off the edge.

As Troy walked down the halls, greeting everyone who talked to him, his two best friends, Chad and Zeke, walked alongside him. They both were on the basketball team as essential players although Zeke did spend as much time in the kitchen as on the court. Gabriella snapped back from her gazing as she heard Taylor scoff.

"Sharpay, are you freaking serious? He's just a typical playboy who egotistical and narcissistic, just like every other guy at this lame-ass school," Taylor said, rolling her eyes and turning around, putting her attention back to his locker.

Sharpay glared at Taylor, taking her eyes off of Troy for a moment. Gabriella did the same.

"Tay, you must be blind. He is drop-dead GORGEOUS! God, I'm just screaming 'Fuck me!' in my head," she retorted. Taylor fake vomited.

Sharpay glanced at Troy again, doing a double take. She squealed, shaking Gabriella's arm furiously.

"Ow, ow, OW! Sharpay, what the hell?" Gabriella exclaimed, pulling herself away from Sharpay's death grip and rubbing her arm.

"He's coming this way, OH MY GOD! How do I look? Hot? Hot. Good," Sharpay quickly said.

Gabriella inhaled sharply and turned around to see blue orbs looking down at her. "Sharpay, Taylor," Troy said, his voice melting Gabriella's insides. He nodded his head at both of them, sending Sharpay to go completely insane. Troy paused as he looked down at Gabriella, smiling at her. "Gabriella," he greeted, winking at her.

Gabriella jumped, a little startled at his gesture, but she kept her cool. "Troy," she greeted.

Chad put his hand on Troy's shoulder, looking at the girls. "So, you girls coming to the homecoming game? With Hoops here, we're going to definitely win. _And_ there's gonna be a huge-ass party afterwards."

"We'll be there!" Sharpay quickly answered. Gabriella and Taylor slowly turned their heads to glare at her. "Heheh, Sharpay. Me and Gabriella have practice that day," Taylor said.

"Psh," Sharpay replied. "Just skip it. You'll have other practices," she shooed Taylor, putting her attention back to Troy.

"We can't just skip, it's a mandatory pra-!" Taylor tried to argue, but Gabriella pinched her, making her shut up.

"_Of course _we can go. We wouldn't want to leave our _best friend alone _now, would we?" she said, making it super obvious to Taylor. Taylor sighed but decided to just listen to Gabriella. There was no use going against Sharpay once her mind is set on something.

"Great, we'll see you there," Zeke said. He high-fived Chad as they walked away with Troy, without taking a couple glances at the girls.

Once the boys were out of earshot, Sharpay practically screamed. "Gabriella, you HAVE to set me up with him. He is my fucking soulmate for God's sake!"

Gabriella widened her eyes. Wait, did she just say what I think she said? "Sharpay, were you NOT listening to me in the car? No more matchmaking for me! No, none, NADA! Got it?" she said very loudly and clearly.

Sharpay frowned. "Come on! Please. It'll be your last matchmaking. I won't let you join the musical. I'll.. pay you! Come on, it's Sharpay - one of your best friends here! It's only one tiny favor. Besides, I've done a lot for you!" she pleaded.

"Actually-," Gabriella started but Sharpay stopped her to glare at her. Gabriella sighed and turned to look at Taylor who just shrugged. "Why not?" Taylor said.

Gabriella turned to look at Sharpay and bit her lip. She heavily sighed and slowly nodded her head. "Alright, fine. But you'll listen to exactly EVERYTHING I say and OBEY ME, got it?" she instructed. Sharpay nodded her head like a puppy dog.

Sharpay closed her locker and grabbed Gabriella in a huge bear hug. Gabriella grunted but managed to close her locker as the bell rung, walking to homeroom with Taylor giggling behind them.

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><p><strong>AN: Okay, that's the first chapter! I hope you liked it. Don't worry, I'll make a chapter for how Gabriella got started in the matchmaking business and all that. Still unknown if I'll write in Troy's perspective (well, I kind of have to), but we'll see where we go. Don't forget to review! xoxo<strong>


	2. Homecoming Game

**AN: So, I'm bored, it's almost 2am and I want to write more chapters to my fanfic. Yuppers, hope you enjoy! P.S. Sorry if things are a bit slow, but, you know, gotta start somewhere.**

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><p>Friday night: the homecoming basketball game. The first basketball game in the season and who were they up against? They're arch-rivals, West High - the home of the Wolves. But of course, Troy and everyone else weren't scared. Well, at least on the outside they weren't.<p>

The game was coming to an end with 50 seconds left on the clock. East High was down by two points at 36 - West at 38. Troy was dribbling the ball down the court, waiting for an opening. He was drenched with sweat, but he had no problem still looking wildly attractive.

Coach Bolton was yelling at the players from the sidelines. He was ready to pull his hair off. The cheerleaders were obviously cheering, doing kicks and jumps to encourage them. Gabriella just rolled her eyes at the sight of them. Sharpay was screaming her head beside her, screaming "TROY!" every five seconds, hoping that he would at least glance at her (which she didn't). Everyone was standing up, jumping and cheering in anticipation. Taylor was seating next to Gabriella, probably the only one standing. Her legs and arms were crossed, not pleased at the fact that she was here (although she still managed to wear red and white for school spirit).

Gabriella was just slowly clapping her hands, smiling. The game captivated her and she soon got into it as everybody else. 30 seconds left, Troy was boxed in, nobody to pass to. 28 seconds left, still nobody.

Chad came out of nowhere, yelling Troy's name and getting his attention. He successfully got the ball and did a nice dunk. The two teams were now tied.

As East High ran back to their side of the court, Sharpay was grabbing onto her arm again, digging her nails into her skin. "Gabriella, I'm so nervous!" Sharpay squealed. Gabriella rolled her eyes but kept her attention on the game. One of West's players dribbling down the court but had managed to travel. The referee blew his whistle, giving East High the chance for some free throws. With both teams on the sides of the key, Troy was at the free throw line, getting ready to shoot. 10 seconds left - all he needed to do was make one shot and they would win the game.

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><p>Troy breathed heavily, blowing his chest with his jersey. One of West's players had traveled so Troy was chosen to do the free throw shot. 10 seconds left - absolute pressure from both crowds, the team, AND his father made him want to disappear. As he stood behind the line, he bounced the ball a bit. The audience hushed as they waited in anticipation for the shot to be made. Troy gulped.<p>

Getting into position, Troy stared at the hoop. He prayed in his mind, before making the shot. It seemed that time has slowed as he watched the ball fly through the air. He bit his lip. "Please, please, please.." he mumbled to himself. Closing his eyes, not wanting to see, he heard the buzzer ring. Silence.

Troy felt disappointed, he didn't make it. He left the whole school down and lost to their arch rivals in the FIRST game of the season.

But then, cheers. Loud cheers. He opened his eyes in surprised as his teammates jumped around him. He stared wide-eyed at the hoop, the ball falling down from the net. His mouth was gaped open.

"YEAH!" he heard, being lifted up in the air. "Troy! Troy!" everyone chanted, cheerleaders and people from the stands surrounding him. He smiled widely to himself and threw his hands up in the air.

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><p>Gabriella screamed as the buzzer blew and the ball fell through the hoop. "WE WON! WE WON!" Sharpay screamed and jumped, Gabriella joining in with her. Gabriella nudged Taylor, who said a sarcastic "Woohoo."<p>

She rolled her eyes and just smiled to herself, glad that they won.

x o x o x o x

Gabriella slammed the car door behind her. Taylor got out as well and stood next to her. They both exclaimed when they saw the house before them. It was huge. There were cars parked on the grass and driveways, hundreds of students gathered around. It was the party of the century and school JUST started.

"Come on!" Sharpay called before them, pulling them out of their trance. "We've gotta find Troy!"

Taylor rolled her eyes and Gabriella just giggled. Pulling her arm, Taylor led them towards the kitchen where she found Sharpay and Troy talking.

Troy noticed Taylor and Gabriella and smiled. "Hey, you guys made it!" he said. Taylor ignored him and just walked by Sharpay's side.

"Well you know us, we'll be here when a friend needs us," Gabriella said, glancing at Sharpay.

"What, so you wouldn't be here if Sharpay wasn't here?" he asked.

Gabriella squinted her eyes a bit, nodding her head like she was thinking. "Not.. exactly. See, I'm more of a studying than a partying-kind of girl," she answered.

"Ahh, I get it. But, aren't you more of a matchmaker than a brainiac?" he retorted cleverly.

Gabriella giggled. "So the word's spreading, huh? Well, unfortunately for you, I'm retired." Sharpay hit her on the arm, _hard. _

Gabriella mouthed an "Ow!" but got that hint. "-I mean! Will be, I will be retiring," she quickly corrected herself, smiling nervously.

"Sharpay!" a familiar male voice called. Gabriella turned her head to see Ryan, Sharpay's twin brother.

"What Ryan? Can't you see I'm busy," Sharpay said angrily, trying to get him to leave.

Ryan nodded his head towards Troy but continued talking to Sharpay. "They've got karaoke and we've gotta show them how we do things~."

Sharpay gasped and smiled. Touching Troy's arms, reassuring she'd be back, and ran towards the living room with Ryan, Taylor following her leaving Gabriella alone with Troy.

"She must reaally like singing," Troy said.

Gabriella sighed. "You have **no** idea." Looking up at Troy, she felt his sapphire eyes entering her soul. She took a step back reluctantly, but blushed at her action. "Um, so.. oh yeah, congratulations!" she said, totally forgetting was the party was for.

"Hah, thanks. It was really.. nerve-wrecking," he replied, grinning at her. He scratched the back of his neck.

"So, I'm guessing all of the cheerleaders are alll over you," she said.

"Yeah.. I'm not really interested."

Gabriella lit up - this was her chance. "Oh really? Why not?" she asked him.

"Well, they're not really not my type."

"What is your type, then?"

"A girl who's.. down-to-earth. Passionate for what she does and happy with herself," he said, smiling to himself. "A girl with a cute laugh, someone who can make me smile. A girl I can not only care for and love, but joke and tease with."

Gabriella was slightly taken back at his words. Yeah, she knew he was a little different but she didn't know he was THAT different. She gulped, he was going to be a toughy.

"That was really.. in depth," she replied.

He chuckled. "Well, I'm a picky eater."

Gabriella raised an eyebrow. As she was about to talk, Sharpay came running back in, Taylor following her lead.

"Troy! I had the BEST time singing. They loved me!" Sharpay squealed. A lightbulb went off in Gabriella's head and smiled to herself.

"Wow, Sharpay, you must be _really _passionate about singing."

"Of course I am! I live and breath for singing. Just being in front of the crowd and singing my heart out," she said, sighing. "It's a thrill."

Gabriella took a moment to glance at Troy's face. He was staring at Sharpay with an impressed and astonished look. He noticed Gabriella was looking at him so she stared at the ground and blushed.

"Um, hey, Taylor," Gabriella said, breaking the silence. "I think I left something in the car. Sharpay, can I borrow your keys?" Gabriella said, looking at Sharpay.

"Oh, yeah sure!" she replied, taking them out of her purse and into Gabriella's hand. As soon as she did that, she pulled Taylor out the front door and towards the car.

"Whoah, slow down there girl," Taylor said as they stopped in front of the car. "What was that for?"

"Matchmaking," she replied, opening the door to the driver's seat and getting in, Taylor sitting next to her. "We are going to leave while Sharpay talks it up with Troy."

As they both put on their seatbelts and Gabriella started the car, Taylor asked, "Wait, then how is she going to get home because Ryan left after karaoke."

"Simple: Troy'll drive her home," she said, smiling at Taylor before pulling out and driving away.

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><p>Sharpay was in an in-depth conversation with Troy about their hobbies and futures. Just then, she felt a vibration in her pocket. Excusing herself, she saw it was a text from Gabriella that said:<p>

**FROM: Gabriella**

**To: You**

**I took your car keys and we're at my house. Get Troy to drive you home. Also, he likes down-to-earth girls who are passionate. Laugh cute and make him smile - good luck!**

**xox Gab**

Sharpay flipped her phone shut and was mouth wide-open. Gabriella sure worked fast. Turning her attention back to Troy, she was smiling to herself, doing what Gabriella had instructed. Let the games begin.


	3. Round One

Taylor ended up staying over that night after they had ditched Sharpay at the party. It was already 9PM the next day and Gabriella and Taylor were having a horror and chick flick movie marathon.

As their eyes were glued to the screen, each inching closer to each other with their fear increasing. The screen was zooming in on the front door, the main protagonist walking slowly towards it to turn the knob.

As soon as her hand, touch the knob and continued to turn..

The door bell rang - which made Taylor and Gabriella fill her house with screams. Popcorn was thrown into the air and back onto their laps and hair.

Taking a minute or two to catch their breath and regulate their heart rates, Taylor paused the movie as Gabriella got up from the couch to open the door.

As soon as the door was an inch open, Sharpay pushed it open sending Gabriella to almost stumble backwards.

"I had the BE-EST time last night," Sharpay squealed, stealing's Gabriella's seat next to Taylor, popping a piece of popcorn in her mouth.

"Oh, I'm oozing with excitement," Taylor replied sarcastically, rolling her eyes. She adjusted her self on the couch to feel comfortable.

Gabriella giggled and closed the front door, jumping down onto the couch next to Sharpay. "So, the deets Ms. Evans?"

"Okay, so once I got your text and we went into this _huge _conversation about the greatest topics," Sharpay started. "Then, we started dancing and walked around in the backyard." She squealed again.

"So, after that, Chad told Troy to check out out back where the basketball court so he excused himself, what a gentleman, and left me there in the kitchen waiting for him." Sharpay sighed. "So, I was going to walk out because he had been gone for a while but there was this puddle of soda on the floor that I didn't see and I slipped on it!" Taylor and Gabriella dramatically gasped.

"I know, right? Anyway, I thought I was going to go down and totally embarrass myself but then guess who came out of no where to save me?"

Taylor and Gabriella both had blank faces on, acting like they didn't know.

Sharpay groaned. "Troy!" Taylor rolled her eyes again but couldn't help but smile at her best friend's success.

"So, as I was slipping, he caught me and held me up and, oh my god, we_ totally _had a moment." Sharpay sighed and leaned farther into the cushions of the couch.

"Did he ask you out on a date?" Taylor asked.

Sharpay bit her lip, sitting up straight again. "Here's the thing.. after he drove me home, he said good-night, we hugged but.. that was it! Not even a kiss on the cheek!" she exclaimed. She turned to face Gabriella. "Gabs, what did I do wrong?"

Gabriella sighed and leaned back. "Nothing, you did everything perfect. It's him that wrong." Sharpay was going to object but Gabriella sent her a 'not-what-I-meant' look that made her stay quiet.

"That boy is a tough cookie. It's going to take more than my normal tactics to get him to fall for you," she admitted. Gabriella hit her knees as she stood up, turning to face both Taylor and Sharpay with serious expressions.

"Okay, girls. Our plan is just about to begin."

"Wait, didn't it already begin?" Taylor asked.

"That was practice. Now, serious business is going to start. Phase one of Plan 'Get Sharpay and Troy together' activate!" Gabriella exclaimed.

Sharpay jumped up and clapped her hands, a ridiculous smile on her face.

Taylor just rolled her eyes but sighed and stood up next to her. "So.. the plan, boss?"

x o x o x o x

"Okay kids, we have 10 minutes 'till the bell rings so let's talk about your projects, okay?" the teacher stated. There were groans throughout the classroom. "You will work in pairs. You are assigned a historical figure to research over the next 2 weeks. You will then present it to the class and will be graded at that time."

Gabriella pouted as she glanced behind her should, surveying the class. It was her only period where she didn't have either Taylor or Sharpay with her so finding a partner would be hard. She then noticed Troy talking in the back with one of his friends. A lightbulb went off in her head as she grinned to herself and looked back at the teacher.

Just then, the bell rang. "Okay, make sure you have your partners are chosen by tomorrow! We'll talk more later," the teacher stated. Gabriella gather up her books, holding them by her side as she put her backpack strap on.

She scurried out of the classroom and was glad as she saw Troy's friends disperse from their circle around him. Finding him alone, she took a deep breath as she walked up to him. "Troy!"

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><p>"See you later, man," Troy said. Walking down the hall, he heard his name being called. Stopping to turn around, he found Gabriella walking towards him. "Oh, hey Gabriella," he greeted.<p>

"Hey," she replied, walking next to him now, struggling to keep her books in place. Troy couldn't help but smile.

"So um, have you got a partner for the History project, yet?" she asked.

Troy bit his lip. "Ah, not yet actually, I'm still choosing."

"Oh.. well, want to be my partner?" she said, looking down at the ground.

Troy was taken back, surprised that she asked him. She could have easily found a partner that was at her intelligence level. "Um, are you sure? I might drag you down."

"No, no, no! It's fine. Well, I mean, you're the only person I know in class, so.." she trailed on.

Troy chuckled, rubbing the back of her neck. They stopped outside of her next class. He looked down at her. Her chocolate brown orbs made his insides melt, making him just kiss right then and there. But he couldn't, no. She obviously didn't like him, not in a million years.

"Yeah, sure. I'll be your partner."

"Great! I'll see you tomorrow after school? Library?" she said, walking towards the entrance.

"I'll be there," he winked as she watched her walk into her classroom. He smiled to himself, standing there for a moment. Taking one last glance into the classroom, he hurried off to his next period.

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><p>Gabriella walked into Sharpay's bedroom which was, you guessed, pink-infested. She sighed and sat down on her bed, throwing her bag down on the floor next to the door.<p>

Sharpay sat in one of the chairs in front of the bed, by her flat-screen TV. "I hate school."

Taylor tsk'ed. "Don't be ridiculous," she said, sitting down next to Gabriella.

"I got some news on Troy," Gabriella stated.

Sharpay mini-screamed as she jumped up to sit down in front of Gabriella. "What is it?" she asked eagerly.

"Well, he's my partner in this project that we're doing in History and we'll meet after school tomor-" Sharpay gasped. "Don't. I don't like him so don't be worried."

"Anyway, so I'll meet him after school and I'll try my best to get to know as much about him as possible." Sharpay jumped up and down on the bed.

"AH! Gabriella, you are a miracle worker!" she said, holding her hand. "I can already see it, us married in our huge villa. I've already named our kids!"

Taylor hit Sharpay upside of her head with her math binder. "Okay, enough daydreaming. We've got homework to do? Remember?"

Gabriella giggled and sighed, taking out her binder to work on. She was kind of worried though. Gabriella might lead Troy on, but she'll just have to work ten times harder to get this right. She has to, it's for Sharpay. She sighed.


End file.
